• 공업화학
• /
• 제16권6호
• /
• pp.834-841
• /
• 2005

아디픽산 및 세바식산의 이염기산을 폴리에틸렌글리콜(PEG)과 축합 반응하여 여러종류의 PEG-ester를 합성하였다. 합성된 PEG-ester의 화학적 구조 및 분자량을 FT-IR, $^1H-NMR$, HPLC 및 GPC에 의하여 분석하였다. 또한, 임계미셀농도(CMC), 표면장력, 알루미늄판에 대한 접촉각 등을 통하여 수용액상에서 계면활성제의 역할을 함을 알 수 있었다. PEG-ester의 농도에 따라 표면장력은 72.5에서 45~50 dyne/cm로 감소함을 알 수 있었고, 세바식산을 사용하여 합성한 PEG-ester가 아디픽산을 사용하여 합성한 PEG-ester보다 같은 농도에서 낮은 표면장력을 나타내었다. CMC는 구조에 따라 차이를 나타내었는데 세바식산을 함유한 PEG-ester의 CMC는 $0.9{\times}10^{-5}{\sim}5.3{\times}10^{-3}mol/L$로 폴리옥시알킬렌 단위체가 길어질수록 증가하였으며 아디픽산을 함유한 PEG-ester의 경우, 변곡점을 뚜렷하게 관찰할 수가 없었다. 알루미늄에 대한 젖음성을 알루미늄 시편에 대한 접촉각을 측정하여 검토하였는 바, PEG-ester의 농도가 증가할수록 작아짐을 알 수 있었고 임계점을 관찰할 수가 있었다. 2.5 wt% PEG-ester를 함유한 수용액의 알루미늄에 대한 접촉각은 $45{\sim}53^{\circ}$이었으며 알루미늄 가공 절삭시간은 CMC를 나타내는 농도에서 가장 짧게 관찰되었으며 CMC 농도보다 큰 농도에서 길게 나타났다. 즉, 알루미늄을 가공할 때 PEG-ester의 CMC가 절삭성능에 중요한 영향을 미치는 것으로 판단되었다.

• 약학회지
• /
• 제29권5호
• /
• pp.234-245
• /
• 1985

To clarify the diffusional behavior of p-aminbenzoic acid esters in the presence of polyethylene glycol 400, cellulose membrane permeation rate, solubility and viscosity of p-aminobenzoic acid methyl ester, benzocaine and butamben were determined with PEG solutions of various concentrations. With an increase in PEG concentrations permeation rates from solutions; decreased due to an increase in viscosity of the solution. From suspensions, however, permeation rates increased due to an increase in solubility and when the initial drug concentration was constant, permeation rates were found to be greatest from the PEG-water system with the PEG concentration which transported from the solution to the suspension. Permeation rate of 4.0mg/ml p-aminobenzoic acid methyl ester was $26.51\mu$g/ml$\cdot$hr from 5g/100ml PEG solution, and that of 4.0mg/ml benzocaine was $13.17{\mu}g/ml{\cdot}hr$ from 15g/100ml PEG, solution, and that of 2.0mg/ml butamben was $3.8{\mu}g/ml{\cdot}hr$ from 10g/100ml PEG solution. Permeation rate was 7.0 fold in p-aminobenzoic acid methyl, ester and 3.5 fold in benzocaine compared to butamben.

• Archives of Pharmacal Research
• /
• 제27권8호
• /
• pp.878-883
• /
• 2004

Tacrolimus (FK506), which is isolated from Streptomyces tsukubaensis, is a new potent immu-nosuppressant. Because of poor solubility in water, the conventional intravenous dosage forms of tacrolimus contain surfactants such as cremophor EL (BASF Wyandotte Co.) or hydroge-nated polyoxy 60 castor oil (HCO-60) which may cause adverse effects. This study relates to a polymer-tacrolimus conjugate, which can be dissolved in water, formed by chemically binding the sparingly soluble drug, tacrolimus, with the water soluble polymer, methoxypoly(ethylene glycol) (mPEG). Water soluble tacrolimus-mPEG conjugates have been synthesized and shown to be function in vitro as prodrugs. These conjugates are in the form of an ester wherein the 24-, 32- or 24,32-positions are esterified. The desired 24-, 32- or 24,32-esterified com-pounds were obtained by initially acylating of tacrolimus with iodoacetic acid at the 24-,32-, or 24,32-positions and then reacting the resulting acylated tacrolimus with a mPEG in the pres-ence of a base such as sodium bicarbonate. These conjugates were converted again into tac-rolimus by the action of enzymes in human liver homogenate, and the half-lives of the conjugates are approximately 10 min in the homogenate, indicating that the esterified tacroli-mus derivatives may be practically applicable as a prod rug for the immunosuppressant.

• Biomolecules & Therapeutics
• /
• 제19권1호
• /
• pp.109-117
• /
• 2011

In this work, we have investigated the effect of polyoxyethylene alkyl ester nonionic surfactants on percutaneous permeation enhancement of a model drug, ketoprofen. We also investigated the mechanism involved in the enhancement using impedance and solubility measurement. Three groups of nonionic surfactants with different ethylene oxide content were studied. The permeation results showed that all surfactants enhanced the percutaneous absorption, irrespective of the molecular weight. The permeation results from PEG-45 monostearate (PEGMS45) were rather unexpected. Impedance and solubility results indicate that the mechanism involved in the enhancement of permeation by PEG-10 monooleate (PEGMO10) and PEGMS45 is rather different. The results from PEGMS45 suggest that it could be a potential candidate as a skin penetration enhancer with high molecular weight, which may poses less skin irritation and systemic side effect than the smaller surfactant molecules. Overall, this work provided some useful information on percutaneous transport enhancement and the mechanistic insights involved in skin permeation for these nonionic surfactants.

• Macromolecular Research
• /
• 제15권5호
• /
• pp.437-442
• /
• 2007

Poly(ethylene glycol) methyl ether (PEG)-poly(${\beta}$-amino ester) (PAE) block copolymers were synthesized using a Michael-type step polymerization, and the construction of pH-sensitive polymeric micelles (PM) investigated. The ${\beta}$-amino ester block of the block copolymers functioned as a pH-sensitive moiety as well as a hydrophobic block in relation to the ionization of PAE, while PEG acted as a hydrophilic block, regardless of ionization. The synthesized polymers were characterized using $^1H-NMR$, with their molecular weights measured using gel permeation chromatography. The $pK_b$ values of the pH-sensitive polymers were measured using a titration method. The pH-sensitivity and critical micelle concentration (CMC) of the block copolymers in PBS solution were estimated using fluorescence spectroscopy. The pH dependent micellization behaviors with various bisacrylate esters varied within a narrow pH range. The critical micelle concentration at pH 7.4 decreased from 0.032 to 0.004 mg/mL on increasing the number of methyl group in the bisacrylate from 4 to 10. Also, the particle size of the block copolymer micelles was determined using dynamic light scattering (DLS). The DLS results revealed the micelles had an average size below 100 nm. These pH-sensitive polymeric micelles may be good carriers for the delivery of an anticancer drug.

• Bulletin of the Korean Chemical Society
• /
• 제26권7호
• /
• pp.1079-1082
• /
• 2005

The purpose of this study was to develop a method for increasing the solubility of paclitaxel in water to reduce its toxicity and make the drug more feasible for chemotherapy. A series of highly water soluble paclitaxel polyethylene glycol (PEG) esters were synthesized and evaluated for their anti-tumor activity and toxicity. The solubility of 7-polyethylene glycol paclitaxel carbonate 5 was 840 mg/mL and the acute toxicity ($LD_{50}$) was 286 mg/kg. Because of its reduced toxicity, compound 5 showed a dramatic reduction of tumor volume without any loss of animals in long-term treatment (daily consecutive injections for 15 days).

• 대한화장품학회지
• /
• 제30권3호
• /
• pp.369-375
• /
• 2004

제미니형 계면활성제를 사용하여 액정을 제조하였으며 보습효능을 측정하였다. 계면활성제로는 디코코일에틸렌디아민(PEG) -15설페이트 (SCD-PEG-15S) $3.0\;wt\%$와 부스터로는 수소첨가 다이머에씨드에스터(HDAE) $4.0\;wt\%$를 사용하였다. 안정화제로 베헤닐알코올(BA) $2.0\;\;wt\%$와 리소레시친(LyL) $1.0\;wt\%$를 사용하였다. $pH 4.0{\~}10.5$ 범위에서 안정하였으며 최적조건은 6.5이었다. 가장 안정한 상태의 점도는 $8,000{\pm}500$ cP이었으며. 입자크기는 4.0에서 15.5 um 범위에서 가장 잘 형성되었다. 입자의 모양과 구조는 편광현미경을 통하여 관찰하였으며, LC의 입자 주변에 액정이 형성되었음을 확인하였다. 또한 액정의 입자주변에 겔 네트워크 구조를 형성하고 있다는 것을 알 수 있었다. 시료도포 후 30 min 경과후의 보습효과는 control보다 $13.6\%$ (P<0.05) 증가함을 보였으며, 1 h 후의 보습효과는 control보다 $12.6\%$ (P<0.05) 증가함을 보였다. 또한 4 h 후의 보습효과는 control보다 $28.3\%$ (P<0.05) 증가하였다. 이는 제조한 액정이 라멜라형 구조를 형성하여 수분 포접력과 오일의 흡착력 증가로 인한 효과로 판단된다. 향후 피부의 전달체계(delivery system)에의 적용이 가능하고 나아가 의약이나 제약, 화장품 등을 만드는데 응용될 것으로 기대된다.

• 한국응용과학기술학회지
• /
• 제36권4호
• /
• pp.1443-1459
• /
• 2019

리글리세린지방산에스터 비이온계면활성제는 식품 등에 오래전부터 사용해 왔으며 PEG계 비이온계면활성제의 안전성 문제에 대한 대안으로 제시되고 있다. 폴리글리세린지방산에스터 계면활성제는 친수기인 폴리글리세린과 친유기인 지방산을 결합시켜 합성된다. 친수기인 폴리글리세린은 글리세린, 글리시돌, 에피클로로히드린 등을 이용하여 중합되는 데 폴리글리세린 중합반응의 주요 이슈는 분기·환상형태가 아닌 직쇄형태의 폴리글리세린의 함량을 높이고 중합도의 분포를 좁히는 것이다. 친수기인 폴리글리세린에 지방산계 친유기를 결합시키는 방법에는 에스터화 반응 등의 화학적 합성법과 지방분해효소를 이용한 효소 합성법이 있다. 폴리글리세린지방산에스터 합성의 주요 이슈는 에스터화정도를 조절하면서 반응수율을 높이고 부반응을 억제하는 것이다.